1. Field of the Invention
This invention relates to a method of producing 1,9-nonanedial and/or 9-hydroxy-7-nonen-1-al. More particularly, the invention relates to a method of producing 1,9-nonanedial and/or 9-hydroxy-7-nonen-1-al which comprises reacting 2,7-octadien-1-ol with a mixture of hydrogen and carbon monoxide in the presence of a catalyst.
2. Description of the Prior Art
1,9-Nonanedial is useful as a protein- or enzyme-immobilizing agent, a microbicidal agent, or a starting material for the production of industrially valuable compounds such as azelaic acid, 1,9-nonanediol and 1,9-nonanediamine. Prior to the present invention, however, advantageous methods for producing 1,9-nonanedial have not been developed and accordingly 1,9-nonanedial has not yet been produced on a commercial scale. An example of a conceivable process for producing 1,9-nonanedial would comprise subjecting oleic acid to ozonolysis, esterifying the resulting azelaic acid and subjecting the azelaic acid ester to half reduction with lithium aluminum hydride. However, such a process would have such drawbacks as difficulty in selective production of 1,9-nonanedial by half reduction and high costs of starting material and reducing agent, and consequently would be impractical from the commercial viewpoint. A commercially advantageous method for the production of 1,9-nonanedial using an inexpensive starting material has previously been unavailable.